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Hydrogen-Bonding-Regulated Morphology Control and the Impact on the Antibacterial Activity of Cationic π-Amphiphiles.
- Source :
-
Langmuir : the ACS journal of surfaces and colloids [Langmuir] 2024 Jul 09; Vol. 40 (27), pp. 13870-13878. Date of Electronic Publication: 2024 Jun 25. - Publication Year :
- 2024
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Abstract
- This manuscript describes the synthesis, self-assembly, and antibacterial properties of naphthalene-diimide (NDI)-derived cationic π-amphiphiles. Three such asymmetric NDI derivatives with a nonionic hydrophilic wedge and a guanidine group in the two opposite sides of the NDI chromophore were considered. They differ by a single functional group (hydrazide, amide, and ester for NDI-1, NDI-2, and NDI-3, respectively), located in the linker between the NDI and the hydrophilic wedge. For NDI-1, the H-bonding among the hydrazides regulated unilateral stacking and a preferential direction of curvature of the resulting supramolecular polymer, producing an unsymmetric polymersome with the guanidinium groups displayed at the outer surface. NDI-3, lacking any H-bonding group, exhibits π-stacking without any preferential orientation and generates spherical particles with a relatively poor display of the guanidium groups. In sharp contrast to NDI-1, NDI-2 exhibits an entangled one-dimensional (1D) fibrillar morphology, indicating the prominent role of the H-bonding motif of the amide group and flexibility of the linker. The antibacterial activity of these assemblies was probed against Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). NDI-1 showed the most promising antibacterial activity with a minimum inhibitory concentration (MIC) of ∼7.8 μg/mL against S. aureus and moderate activity (MIC ∼ 125 μg/mL) against E. coli . In sharp contrast, NDI-3 did not show any significant activity against the bacteria, suggesting a strong impact of the H-bonding-regulated directional assembly. NDI-2, forming a fibrillar network, showed moderate activity against S. aureus and negligible activity against E. coli , highlighting a significant impact of the morphology. All of these three molecules were found to be compatible with mammalian cells from the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) and hemolysis assay. The mechanistic investigation by membrane polarization assay, live/dead fluorescence assay, and microscopy studies confirmed the membrane disruption mechanism of cell killing for the lead candidate NDI-1.
- Subjects :
- Microbial Sensitivity Tests
Naphthalenes chemistry
Naphthalenes pharmacology
Imides chemistry
Imides pharmacology
Cations chemistry
Cations pharmacology
Humans
Anti-Bacterial Agents pharmacology
Anti-Bacterial Agents chemistry
Anti-Bacterial Agents chemical synthesis
Hydrogen Bonding
Staphylococcus aureus drug effects
Escherichia coli drug effects
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5827
- Volume :
- 40
- Issue :
- 27
- Database :
- MEDLINE
- Journal :
- Langmuir : the ACS journal of surfaces and colloids
- Publication Type :
- Academic Journal
- Accession number :
- 38917360
- Full Text :
- https://doi.org/10.1021/acs.langmuir.4c00889